


First Time.

by crusadingqueen



Series: Submissive Oliver. [1]
Category: Arrow (TV 2012)
Genre: Anal Fingering, Anal Sex, Dom/sub, F/M, Light BDSM, Mistress, Pegging, Sexual Content, dom!felicity, sub!oliver
Language: English
Status: Completed
Published: 2015-05-07
Updated: 2015-05-07
Packaged: 2018-03-29 10:43:00
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,299
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3893386
Author URL: https://archiveofourown.org/users/crusadingqueen/pseuds/crusadingqueen
Summary: <blockquote class="userstuff">
              <p>Felicity was pulling back causing him to follow her movements, '' No! No! '' He cried out incoherently. Felicity hips stilled to Oliver disappointment but then he realize what he had said.</p><p>'' Don't stop, please don't fucking stop '' He rambled as his hips thrusted back onto the dildo. </p><p>((((READ THE TAGS PEOPLE BEFORE READING THIS! ))))</p>
            </blockquote>





	First Time.

Her hands were slippery and warm as they ran down his shoulder gently massaging the strained kinks that had formed before proceeding downward. His breathing was labored as her hands traveled went lower.  
  
She stopped at the small of his back her thumbs digging into the flesh there drawing small comforting circles. 

'' Are you sure you want to do this? It's okay if you're not ready.. '' She reassured warmly. 

They had been discussing and preparing for this for a while now. It has always lingered in the back of his mind but he had never been completely comfortable or trust them enough to bring it up to past girlfriends. Until Felicity.  


They had shamelessly explored each other kinks and not once did she make him feel odd or uncomfortable when he fessed up to a not so common ones. She had taken it stride.   
  
Nonetheless he had been nervous to admit that he didn't particular enjoy dominating and was more partial subbing but to his surprise Felicity seemed relieved. She had told him that she didn't want to put him in difficult position since she had assumed because of his past experiences he was more the dominating type but she had been wrong. Things progressed slowly and Oliver had found himself loving every second of it.  
  
It was thrilling and quite therapeutic being able to relinquish control from time to time. They had incorporated bondage and even spanking now and again.  
  
Than one night as he was searching the web he had fallen upon a website with Pegging. The more videos he watched the more his desire to try it grew so the next night he had mentioned it to Felicity. 

That's how he found himself here; sprawled on the bed his rock hard cock resting against the pillow position underneath his hips as Felicity traced his puckered rim with her slick finger. Tentatively she pressed her finger against his hole causing him to gasp and jerk forward his length rubbing against the smooth fabric beneath him.

'' You need to stay still baby, If you move again I will spank you. '' She admonished sternly. 

'' Yes Mistress '' He breathed. Anticipation coursed through him like wildfire he wasn't sure what to expect but he had a feeling it was going to be good.

Suddenly Felicity was pushing her finger passed the rim stretching him. Slowly she moved her finger in and out of him letting him get accustomed to the feeling before picking up pace. His face was pressed against the mattress successfully muffling his grunts.  The sensation wasn't painful just a bit uncomfortable at the beginning but that quickly morphed into something more pleasurable. They had done this few times before so Oliver wasn't a complete stranger to the sensations. 

'' Are you ready for another finger babe? '' Felicity asked to which Oliver eagerly nodded. Gingerly Felicity inserted another digit alongside the first. It felt odd at first that was until Felicity crooked her finger upwards allowing her to brush them against his prostate. 

He was no longer unable to keep the moans at bay as Felicity continued to probe at the sensitive bundle of nerves. His cock was throbbing as precum spilled out from the tip. He felt the familiar warmth spread through him warning him of his fast approaching orgasm. 

'' S-stop. If you keep doing that I am going to cum '' He warned hoarsely. He knew it was better to tell his mistress now than cum without having her permission. Almost immediately Felicity finger drew back causing him to whimper. 

Felicity started to scissoring her fingers opening up the slight sting the stretching cause wasn't completely unpleasant. Her other hand came down to massage his buttcheek coaxing him to relax. 

'' You're such a good boy aren't you baby? '' She cooed softly, her sweet voice causing the tension to bleed out of his muscles. He knew that if at any moment he didn't like it she would stop he had absolutely no doubt in his mind about that. All he had to do was say their safe word and she would stop. 

'' Yes, Just for you Mistress '' He mumbled, as he pushed back onto her fingers. 

She went to do the same action until she was satisfied that Oliver wouldn't be in too much pain. When she extracted her fingers Oliver immediately whimpered at the loss. 

As he glanced behind him he watched as Felicity popped the cap of the bottle of lube and proceeded to drizzle copious amount into her palm before rubbing along the emerald green protruding cock that was nestled between her thigh. The sight alone made his breath hitch. 

She came closer to him before taking placing on hands on ass. 

'' Safe word? '' She always asked not because she feared he had forgotten she knew now that the word was now ingrained into his brain but it was a reminder that he should not hesitate to use it. To date, he never had to.

'' Italian '' He said breathlessly. Felicity smiled softly at him a reassuring look on her face allowing him to relax. 

Gingerly she spread his cheek apart and pressed the blunt head against his rim.

'' Don't tense up okay, I need you to stay as relaxed as possible can you do that for me baby? '' She asked.

He inhaled deeply before answering, '' Yes mistress. '' 

Satisfied she gradually started pushing inside. The burning sensation of his walls stretching caused him to hiss. Felicity thumbs drew circles into his flesh trying to calm him down. 

'' Oliver, Baby, You need to breathe.. '' Felicity reminded him softly, stilling inside him completely allowing him to adjust to intrusion. Oliver took large steady gulps of air  the tension in his muscles dissolving. 

He was growing impatient, he needed her to do something so he turned around and said, '' Please Mistress '' 

Felicity caved to his wishes as she became languidly pulling out before sinking back into his warm heat. The pain quickly started transform into blinding pleasure, the kind that him crying out Felicity name. It felt so good. The tip of the dildo was brushing against his prostate making the sensation even more heightened. 

But than Felicity was pulling back causing him to follow her movements, '' No! No! '' He cried out incoherently. Felicity hips stilled to Oliver disappointment but then he realize what he had said.

'' Don't stop, please don't fucking stop '' He rambled as his hips thrusted back onto the dildo. 

She picked up pace as she fucked him till he was practically shaking. Deep guttural groans were being torn from his throat with each thrust of her hips. His ass clenching drawing her in deeper as he rutted against the pillow. He was so close. The cock was splitting him open and filling him completely was too much.

'' Mistress, I need to cum. Can I cum? '' He asked. He stopped his movements his eyes sealing shut as he tried stave off his orgasm.

'' Yes baby, cum for me '' She murmured sending him spiraling over the edge. It felt like he was on fire every muscles in his bed burning with pleasure. He spilled his seed onto the sheets. His orgasm was so intense it had him sobbing into the sheets. 

Carefully Felicity had pulled out of him and peeled off the strap on before crawling on the bed. She cupped his face in her dainty hands and leaned down to kiss him passionately. 

'' You did so well. '' She mumbled against his lips her thumb running against his cheekbone. 

Oliver grinned sheepishly, '' That was really good. '' He admitted. 

'' The hottest thing I have ever seen '' Felicity said biting down on her bottom lip as she replayed the entire thing in her head.  


They both had came to same conclusion this was going to happen again. and again. and again. 

**Author's Note:**

> I know this is different but idk i always thought this would be hot and i am firm believer that oliver is a sub. what do you guys think? And do you guys want me to start a sub!oliver series? maybe? no? Feedback is lovely.


End file.
